Nipecotic Acid → 1-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

HRID 1648374Notes

Reaction equation

[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1.[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:18]([N:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1)([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19]

Participants

Reactant 2

HCID 4498Nipecotic Acid

HCID 10387Benzyl chloroformate

Product 1

HCID 2343391-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

Procedure

By substantially following the procedures of Example 15, A, 25.0 g (194 mmol) of nipecotic acid was protected with benzylchloroformate under basic conditions to afford 18.0 g (68 mmol; 35%) of analytically pure N-Cbz-nipecotic acid as a white solid.

Sources & evidence

ORD record: ord-83c837061c0c4b64b514c4db22669d78
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05436229

Reaction notes

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